.25; H, 4.75. Found: C, 62.88; H, 4.41.Synthesis of (E)-methyl 2-(2-chloro-6-methoxy-4-((7methoxy-4-oxo-2H-chromen-3(4H)-ylidene)methyl)phenoxy) acetate (5c)A remedy of 7-methoxychroman-4-one (4, 300 mg, 1.68 mmol), methyl 2-(2-chloro-4-formyl-6-methoxyphenoxy) acetate (8a, 435 mg, 1.68 mmol) in MeOH (six ml) was stirred at room temperature for 20 min, although a stream of HCl gas was introduced. After 24 h at room temperature, the precipitation was filtrated, crystallized from MeOH to offer compound 5c as pink solid in 64 yield. m.p. 118121 ; IR (KBr, cm-1): 1767 (C = O), 1750 (C = O); 1H NMR (CDCl3, 400 MHz) : 7.9 (d, J = 9.two Hz, 1H, H5chromanone), 7.7 (br s, 1H, CH-vinylic), six.9 (s, 1H, H3phenyl), six.7 (s, 1H, H5-phenyl), six.six (d, J = eight.eight Hz, 1H, H6-chromanone), 6.4 (br s, 1H, H8-chromanone), five.3 (s, 2H, OCH2CO), four.7 (s, 2H, H2-chromanone), three.87 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 3.83 (s, 3H, OCH3); Anal. Calcd for C21H19ClO7: C, 60.22; H, four.57. Found: C, 60.36; H, four.71.Synthesis of (E)-methyl 2-(2-chloro-6-ethoxy-4-((7-methoxy4-oxo-2H-chromen-3(4H)-ylidene)methyl)phenoxy)acetate (5d)7.eight (br s, 1H, CH-vinylic), six.9 (s, 1H, H3-phenyl), six.6 (br s, 2H, H6-chromanone and H5-phenyl), 6.4 (s, 1H, H8chromanone), five.1 (s, 2H, H2-chromanone), four.6 (s, 2H, OCH2CO), four.two (m, 2H, CH2), four.1 (m, 2H, CH2), three.85 (s, 3H, OCH3), 1.four (m, 3H, CH3), 1.3 (s, 3H, CH3); Anal. Calcd for C23H23ClO7: C, 61.82; H, five.19. Identified: C, 62.01; H, 4.89.Synthesis of (E)-methyl 2-(4-((7-methoxy-4-oxo-2H-chromen3(4H)-ylidene)methyl)phenoxy)acetate (5f)A remedy of 7-methoxychroman-4-one (4, 200 mg, 1.12 mmol), methyl 2-(2-chloro-6-ethoxy-4-formylphenoxy) acetate (8b, 288 mg, 1.12 mmol) in MeOH (4 ml) was stirred at area temperature for 25 min, though a stream of HCl gas was introduced. Immediately after 24 h at room temperature, the precipitated solid was filtrated, crystallized from MeOH to offer pure compound 5d as a pink strong in 52 yield. m.p. 15153 ; IR (KBr, cm-1): 1759 (C = O), 1737 (C = O); 1H NMR (CDCl3, 400 MHz) : 7.9 (d, J = 8.8 Hz, 1H, H5-chromanone), 7.8 (br s, 1H, CH-vinylic), six.Baclofen 9 (s, 1H, H3-phenyl), six.D-Cycloserine six (br s, 2H, H6-chromanone and H5phenyl), 6.four (br s, 1H, H8-chromanone), five.1 (s, 2H, CH2), four.7 (s, 2H, H2-chromanone), four.1 (m, 2H, CH2), 3.85 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 1.five (t, J = 6.8 Hz, 3H, CH3); Anal. Calcd for C22H21ClO7: C, 61.05; H, 4.89. Identified: C, 60.83; H, five.03.Synthesis of (E)-ethyl 2-(2-chloro-6-ethoxy-4-((7-methoxy-4oxo-2H-chromen-3(4H)-ylidene)methyl)phenoxy)acetate (5e)A remedy of 7-methoxychroman-4-one (four, one hundred mg, 0.56 mmol), methyl 2-(4-formylphenoxy)acetate (11c, 109 mg, 0.PMID:23800738 56 mmol) in anhydrous MeOH (2 ml) was stirred at space temperature for 25 min, even though a stream of HCl gas was introduced. Immediately after 24 h at room temperature, the precipitation was filtrated, crystallized from methanol to afford pure compound 5f as a red strong in 71 yield. m. p. 13133 ; IR (KBr, cm-1): 1760 (C = O), 1667 (C = O); 1 H NMR (CDCl3, 400 MHz) : 7.eight (d, J = eight.four Hz, 1H, H5chromanone), 7.6 (s, 1H, CH-vinylic), 7.41 (d, J = eight.eight Hz, 2H, H2- and H6-phenyl), 7.05 (d, J = 8.four Hz, 2H, H3- and H5-phenyl), 6.7 (d, J = 8.two Hz, 1H, H6-chromanone), 6.5 (s, 1H, H8-chromanone), five.4 (s, 2H, OCH2CO), four.eight (s, 2H, H2-chromanone), three.8 (s, 3H, OCH3), three.7 (s, 3H, OCH3); MS, m/z: 354, 295, 281, 265, 253, 151, 131, 115, 77, 63, 45. Anal. Calcd for C20H18O6: C, 67.79; H, five.12; Identified: C, 68.00; H, 4.98.Synthesis of (E)-ethyl 2-(4-((7-methoxy-4-oxo-2H-chromen-3 (4H)-ylidene)methyl)phenoxy)acetate (5g)A sol.